Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives

被引：8
|
作者：
Labana, Balvantsingh M. [1 ]
Brahmbhatt, Gaurangkumar C. [1 ]
Sutariya, Tushar R. [1 ]
Parmar, Narsidas J. [1 ]
Padron, Jose M. [2 ]
Kant, Rajni [3 ]
Gupta, Vivek K. [3 ]
机构：
[1] Sardar Patel Univ, Dept Chem, Vallabh Vidyanagar 388120, Gujarat, India
[2] Univ La Laguna, IUBO AG, Ctr Invest Biomed Canarias CIBICAN, BioLab, C Astrofis Francisco Sanchez 2, San Cristobal la Laguna 38206, Spain
[3] Univ Jammu, Postgrad Dept Phys, Jammu 180006, India
来源：
MOLECULAR DIVERSITY | 2017年 / 21卷 / 02期
关键词：
DKHDA reaction; Ketone-based DKHDA substrates; Benzopyran; Pyrano[2,3-c]pyrazole; Antiproliferative activity;
D O I：
10.1007/s11030-017-9734-y
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A one-pot method has been described to synthesize benzopyran-annulated pyrano[2,3-c] pyrazoles, effectively by combining O-alkenyloxy/alkynyloxy-acetophenones with various pyrazolones in triethylammonium acetate (TEAA) under microwave irradiation. While combination of O-allyloxy-or O-prenyloxy-acetophenones with pyrazolones occurred efficiently, that of O-propargyloxy-acetophenones was found effective in the presence of ZnO catalyst, via a domino Knoevenagel-hetero-Diels-Alder (DKHDA) reaction. Aminobenzopyran frameworks were also synthesized, after nitro-containing products were reduced in tandem with iron(II) in an acidic medium. The in vitro antiproliferative activity of these compounds was measured and discussed against gram-positive, gram-negative and M. tuberculosis bacteria, fungi, and various representative human solid tumor cell lines, in addition to their ferric reducing antioxidant capability.
引用
收藏
页码：339 / 354
页数：16
相关论文
共 50 条
  • [1] Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives
    Balvantsingh M. Labana
    Gaurangkumar C. Brahmbhatt
    Tushar R. Sutariya
    Narsidas J. Parmar
    José M. Padrón
    Rajni Kant
    Vivek K. Gupta
    Molecular Diversity, 2017, 21 : 339 - 354
  • [2] Tetrabutylammonium hydrogen sulfate mediated domino reaction: synthesis of novel benzopyran-annulated pyrano[2,3-c]pyrazoles
    Parmar, Narsidas J.
    Teraiya, Shashikant B.
    Patel, Rikin A.
    Talpada, Navin P.
    TETRAHEDRON LETTERS, 2011, 52 (22) : 2853 - 2856
  • [3] Synthesis and molluscicidal activity of new cinnoline and pyrano [2,3-c]pyrazole derivatives
    Abdelrazek, Fathy M.
    Metz, Peter
    Metwally, Nadia H.
    El-Mahrouky, Sherif F.
    ARCHIV DER PHARMAZIE, 2006, 339 (08) : 456 - 460
  • [4] Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives
    Abdelrazek, Fathy M.
    Metz, Peter
    Kataeva, Olga
    Jaeger, Anne
    El-Mahrouky, Sherif F.
    ARCHIV DER PHARMAZIE, 2007, 340 (10) : 543 - 548
  • [5] An efficient and eco-friendly synthesis and evaluation of antibactrial activity of pyrano[2,3-c]pyrazole derivatives
    Manouchehr Mamaghani
    Roghayeh Hossein Nia
    Farhad Shirini
    Khalil Tabatabaeian
    Mehdi Rassa
    Medicinal Chemistry Research, 2015, 24 : 1916 - 1926
  • [6] An efficient and eco-friendly synthesis and evaluation of antibactrial activity of pyrano[2,3-c]pyrazole derivatives
    Mamaghani, Manouchehr
    Nia, Roghayeh Hossein
    Shirini, Farhad
    Tabatabaeian, Khalil
    Rassa, Mehdi
    MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (05) : 1916 - 1926
  • [7] Magnesium ferrichromate nanoparticles: an efficient and recyclable catalyst in the synthesis of pyrano[2,3-c]pyrazole derivatives
    Yellapurkar, Ishita
    Bhabal, Sonal
    Ramana, M. M. V.
    Jangam, Kundan
    Salve, Vaibhav
    Patange, Sunil
    More, Paresh
    RESEARCH ON CHEMICAL INTERMEDIATES, 2021, 47 (07) : 2669 - 2687
  • [8] Magnesium ferrichromate nanoparticles: an efficient and recyclable catalyst in the synthesis of pyrano[2,3-c]pyrazole derivatives
    Ishita Yellapurkar
    Sonal Bhabal
    M. M. V. Ramana
    Kundan Jangam
    Vaibhav Salve
    Sunil Patange
    Paresh More
    Research on Chemical Intermediates, 2021, 47 : 2669 - 2687
  • [9] Synthesis and Characterization of New Pyrano[2,3-c]pyrazole Derivatives as 3-Hydroxyflavone Analogues
    Urbonavicius, Arminas
    Krikstolaityte, Sonata
    Bieliauskas, Aurimas
    Martynaitis, Vytas
    Solovjova, Joana
    Zukauskaite, Asta
    Arbaciauskiene, Egle
    Sackus, Algirdas
    MOLECULES, 2023, 28 (18):
  • [10] AN EFFICIENT FOUR-COMPONENT SYNTHESIS OF MULTISUBSTITUTED PYRANO[2,3-c]PYRAZOLE
    Ablajan, Keyume
    Maimaiti, Zulipiya
    SYNTHETIC COMMUNICATIONS, 2012, 42 (13) : 1959 - 1966
12345